Azo dye.



UN FEED STATES PATENT OFFICE.

JOHANNES JANSEN AND WILIIELM NEEL'MEIER, or LEVERKUSE1\T,NEAR COLOGNE GERMANY, ASSIGNORS 'IQ FABBENFABRIKEN VORM. FRIEfiR. BAYER & 00., or ELBERFELD, GERMANY, A CORPORATION or GERMANY.

AZO DYE.

No Drawing.

-;T (115 or/rom it may concern:

lmit lcnown that we, JOIIANNESJANSEN ml \i'imiemr Xl-Il-ILMEIl-LR, doctors of philos- E Specification of Letters Patent.

0 11i chennsts citizens-of the G crmanEm pirc, residing, at Lercrlausen, near Cologne,

Germany, have invented new and useful lm is a specification.

Our invention.relatesto the manufacture and production ofnew azo coloring matters capableof dyeing on a inordant.

The new dyestuffs are obtained by comhining the diazo compounds of such orthocont-ain'- ainino 'ihenol derivatives which either ntro groups or halogens or both intro groups and halogens butno sulfonic or car- .hoxylic groups with dieminodiphenylether carhoxylic acids.

s possess the valuable oert hot-they can he dyed on wool to.

also be dyed on :1 chrome moi-dent or acco ding to the after-chroming method.

The dye ng in onebath-is best-done by add:

ing't-he dye with the bichroniate to the bath,

. entering the wtml, boiling, adding acetic acid in small portions andbo' iling again. The new dyestutls are brown todark brown powders. soluble in water generallywith an orange-red color, and soluble ill-(301% centratcd sulfuric acid generally avith a red color, Theyy eld' upon reduction with Stannous 'chl'oridand hydrochloric aci d an. annnophcnol derivative and a trlannnodi phenol and 2.4-d-1annnodlnhcnylether-l-car phenylether carboxylic acid;

In carrying out onrncw process practically recall HOCGCd as follows, the parts bcing by weig it Example I 18.85 parts of (i-chloro-'nitro aqueous solution, which has to be 1 stirred,

with bichroinate in the same bath.

Patented Jan. 10, 1911.

Application filed August 24 1910. Serial No. 578,606.

ogo'us manner on starting from other others;

7 such as 2.4 -'diainil'iodiphcnylethcr 3 caruntil thc combination is finished, offl parts i of 2.4-dianiinodiphenylethr i -carb oxylic acid (melting point 190? (1.) containing 25':

parts of sodium carbonate The drestutt" is precipitated with common salt. 'It- IS hlicred off, pressed and dried.

orange-red color and which is soluble in cona brown pow-'5 dcr whichns soluble in water with an centrated sulfuric acid with a red color. By reduction wlth stannous chlorid and hydro- 1 liox \jllc acid (melting point 225- Other ortho-aininophcnol derivatives may be used, such as 4e-chloro-2-a minop'henol, fi-iiidilllOIO- Q-aminophenol, initro-Q aminophenol, 5- nitro 2- -an1inopl1(nol, picrainic acid 4- cl'1loro-5-nitro 1-3 aininophenoh (3 nitro -lchloro-ii-aininophenol, .-incthyl-Gmitro-tlaniinophenol, 2.4. di'nitro-R-methyl-(i-aminophenol, etc. r We. claim:'

1.. The herein described new azo dyestuffs obtainable from ortho -a1ninophenol substances and dialeinodiphenylcther carboxy'lic acids which dycstuti's are after being dried and pulverized brown powders soluble in water generallrwith -an orange color, soluble in concentrated sulfuric acid gcncr ally with a red coloryiclding upon reduction with stannous chlorid and hydrochloric acid ortho-sininophenol derivatives and trianiimnliphcnylether (!flllhJX} 'llC acids; and i-lyeing wool together with b'ichromale and acid in the same hath brown shades, substantially asdescribed;

2. The herein described new azo dycst'nfi obtainablefrom (i chlorod nim-Emmino- JOl u N was 11351;): {In 5. Winn-inn airman-12:. 1.. 5. 

